Benzoic Acid → 5-Chloro-2-phenyloxazolo[5,4-d]pyrimidine

HRID 1470727Notes

Reaction equation

HRID 1470727 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[N:16]=[CH:15][C:14]([NH2:17])=[C:13](Cl)[N:12]=1>O=P(Cl)(Cl)Cl>[Cl:10][C:11]1[N:12]=[CH:13][C:14]2[N:17]=[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:9][C:15]=2[N:16]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 2577975-Amino-2,4-dichloropyrimidine

Product 1

HCID 149130905-Chloro-2-phenyloxazolo[5,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

7.82 g (64.0 mmol) Benzoic acid and 20 mL POCl3 are stirred together at 100° C. for 30 min. Within 45 min 7.00 g (42.7 mmol) 2,6-dichloro-5-aminopyrimidine are added in several portions. The reaction mixture is stirred for additional 2 h at the same temperature. After that time, the mixture is carefully added to an ice cold aq. NaOH solution. The resulting precipitate is filtered off, washed with water and dried.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-47cdd05759e44723b52903f0d903be09
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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